Synthesis, Structures and Properties of Molecular Conductors Based on Bis-Fused Donors Composed of (Thio)Pyran-4-ylidene-1,3-dithiole and Tetraselenafulvalene

  • Ken-ichi Ishidzu
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Minoru Ashizawa
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Masaki Watanabe
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Takashi Shirahata
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Yohji Misaki
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan

説明

<jats:p>Bis-fused donors composed of (thio)pyran-4-ylidene-1,3-dithiole and tetraselenafulvalene (1a, 2a) and their bis(methylthio) derivatives (1b, 2b) were synthesized. Cyclic voltamograms of all the donors consisted of four pairs of one-electron redox waves, and it was suggested that a positive charge of 1+• and 2+• distributed mainly on the (thio)pyran-4-ylidene-1,3-dithiole moiety. X-ray structure analysis revealed that (1b)PF6(C6H5Cl)0.5 and (2b)PF6(C6H5Cl) formed one-dimensional conducting stacks in which the donors were dimerized or tetramerized. In those salts, intramolecular charge disproportionation of the donors was suggested by X-ray structure analysis and density functional theory (DFT) calculation with UB3LYP/6-31G(d) basis function. A tight-binding band calculation suggested that these materials were band insulators. All the donors gave highly conducting TCNQ (7,7,8,8-tetracyanoquinodimethane) complexes and I3− salts (σrt = 0.3–19 S cm−1 on a compressed pellet) with very low activation energies of 0.017–0.040 eV, while single crystals of (1b)PF6(C6H5Cl)0.5 and (2b)PF6(C6H5Cl) exhibited semiconductive behavior with large activation energies (Ea = 0.16–0.22 eV).</jats:p>

収録刊行物

  • Crystals

    Crystals 2 (3), 1092-1107, 2012-08-09

    MDPI AG

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